Sodium triacetoxyborohydride → HCID 71622844, compound

Participants

Reaction Steps

A mixture of Example 80 (150 mg; 0.35 mmol; 1 eq.), 3-oxetanone (38 mg; 0.52 mmol; 1.5 eq.) and sodium triacetoxyborohydride (74 mg; 0.35 mmol; 1 eq.) in DCE (4 mL) was stirred at 50° C. for 16 hours. The reaction mixture was diluted with DCM, washed with 0.1M NaOH, dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (55 mg, 41%) as white foam. 1H NMR (DMSO-d6) δ 7.41-7.31 (m, 1H), 7.01 (dd, J=11.5, 2.2 Hz, 1H), 6.88 (td, J=8.4, 2.3 Hz, 1H), 5.05-4.95 (m, 1H), 4.85-4.78 (m, 2H), 4.69-4.48 (m, 2H), 4.47-4.37 (m, 2H), 4.37-4.21 (m, 2H), 3.60-3.48 (m, 1H), 2.90-2.70 (m, 1H), 2.84 (s, 1.5H), 2.80 (s, 1.5H), 2.62 (s, 1.5H), 2.59-2.53 (m, 2H), 2.56 (s, 1.5H), 2.42-2.15 (m, 2H), 1.84-1.70 (m, 1H). HPLC (max plot) 99.5%, Rt 2.74 min. UPLC/MS: (MS+) 486.5 ([M+H]+).

Provenance & Evidence